Reaktion #2059

Reaktionsgleichung

2-[2,4-dichloro-5-(2-propynyloxy)-phenyl]-2,4-dihydro-5-(3,4-epoxybutyl)-3H-1,2,4-triazol-3-one

potassium carbonate

→

title product

Ausbeute 36.8%

5,6,7,8-tetrahydro-2-[2,4-dichloro-5-(2-propynyloxy)phenyl]-6-hydroxy- 1,2,4-triazolo[4.3-α]pyridin-3(2H)-one

Ausbeute 36.8%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas warmed
2. 2
   Temperaturat reflux for 2h
3. 3
   Filtrationfiltered
4. 4
   SonstigeThe filtrate was evaporated in vacuo
5. 5
   SonstigeThe crude product was purified by flash chromatography over silica gel
6. 6
   Wascheneluting with a 95:5 v
7. 7
   workup.ADDITIONv mixture of dichloromethane and methanol

Vorschrift

A mixture of 500 mg (1.41 mmol) of 2-[2,4-dichloro-5-(2-propynyloxy)-phenyl]-2,4-dihydro-5-(3,4-epoxybutyl)-3H-1,2,4-triazol-3-one and 563 mg (4.08 mmol) of potassium carbonate in 20 mL of acetonitrile was warmed at reflux for 2h. The mixture was cooled to room temperature and filtered. The filtrate was evaporated in vacuo. The crude product was purified by flash chromatography over silica gel, eluting with a 95:5 v:v mixture of dichloromethane and methanol to give 184 mg of the title product of Step 4 as a pale yellow foam, 1H NMR (CDCl3, 400 MHz) δ 7.5 (s,1H), 7.15 (s,1H), 4.8 (s,2H), 4.45 (broad t,1H), 3.8 (m,2H), 3.0 (m,1H), 2.8 (m,1H), 2.6 (s,1H), 2.2 (s,1H), 2.15 (m,1H), 1.95 (m,1H).

Quelle